Who is Cary Leibowitz? A nice Jewish boy who came of age in suburbia during the Nixon-Ford-Carter years? A gay artist, once a darling of New York’s downtown art scene, who early in his career favored the moniker “Candyass”?

Or is he a self-doubting, self-pitying, self-described schlemiel who over the course of a 30-year career has produced pithy, provocative and often hilarious text-based paintings in which he simultaneously mocks and luxuriates in his nebbishy self?

Whoever Leibowitz is — and he is all of those things and plenty more — Bay Area art aficionados and museum-goers are going to learn a whole lot more about him in “Cary Leibowitz: Museum Show,” the first comprehensive survey of the artist’s work, which opens this week at San Francisco’s Contemporary Jewish Museum and runs through June 25.

Featuring more than 350 original pieces, including paintings, works on paper and his mass-produced multiples (a series of identical objects), the exhibition provides an intimate look at an artist who has thought deeply about the intersection of culture and identity since he was a lonely 10-year-old in Trumbull, Connecticut, looking forward to the arrival each month of Architectural Digest.

“Cary is one of the most interesting artists I’ve ever worked with,” said CJM’s Anastasia James, the associate curator who organized the show. “His work is playful, but very critical and relevant.”

At the root of Leibowitz’s work, James said, is his exploration of his gay and Jewish identities, “about being an outsider in the community.”

Indeed, some of Leibowitz’s most compelling works in the CJM show — such as three of his latex-painted panels, the 1995 “I’m A Jew how ’bout u?!!’’ and the 2001 “Do these pants make me Look Jewish?” and “hi Jewboy” — touch on cultural and religious identity while reflecting on Jewish anxiety over finding community and acceptance. More recent work, such as his 2007 mass-produced Fran Drescher Fan Club knit hat, with a Magen David standing in for the “a” in “Fran,” suggests how American Jewish pride is often manifested in kitsch and cultural icons.

The 53-year-old Leibowitz, who is based in New York and has worked in the art auction world there for many years, said he has always found it difficult to define himself as an artist. Though his work often feels political, personal, philosophical and poetic, “I don’t like to be lumped into categories,” he said in a phone interview. “I make dumb little things … I don’t expect to be [understood] by a huge percent of people.”

The “dumb little things,” such as his 1989 marker- and acrylic-based “Wish Fish Dish Lillian Gish” and 1997 marker- and plastic-based “Sad to Bored” sign, which resembles the standard red and white sign hung on the front door of a business to indicate daily hours of operation, have garnered admirers among collectors and critics alike.

“Candyass taps into the abundant feelings of wretchedness and inadequacy brought about by daily interactions with the external world,” critic Rhonda Lieberman wrote in a 1992 Artforum assessment of Leibowitz’s work. “Candyass obeys the compulsion to market himself … but throws his personal failure to do so into the package at no extra charge.”

Leibowitz, who took on the sobriquet “Candyass” after learning that a gay coworker was bullied with the nickname as a child, is only too happy to enumerate what he views as his manifold failures. “I was a kid who didn’t have friends or played sports,” he said in the interview, in what sounded like a badge of honor.

Yet the artist’s declarations of self-loathing are mitigated by a deep yearning to belong to this world, as hostile as it often appears to be. “There is part of me that wants to be normal in an average, American way,” he said.

“Cary Leibowitz: Museum Show,” through June 25 at the Contemporary Jewish Museum, 736 Mission St., S.F.